EP0315046B1 - Colorants formazane cuivrés réactifs - Google Patents
Colorants formazane cuivrés réactifs Download PDFInfo
- Publication number
- EP0315046B1 EP0315046B1 EP88117890A EP88117890A EP0315046B1 EP 0315046 B1 EP0315046 B1 EP 0315046B1 EP 88117890 A EP88117890 A EP 88117890A EP 88117890 A EP88117890 A EP 88117890A EP 0315046 B1 EP0315046 B1 EP 0315046B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- copper
- so3h
- reactive dyes
- copper formazan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- AOLYLEFSPFALGJ-UHFFFAOYSA-N copper formazan Chemical compound [Cu].NN=CN=N AOLYLEFSPFALGJ-UHFFFAOYSA-N 0.000 title claims description 17
- 239000000985 reactive dye Substances 0.000 title claims description 15
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 19
- 239000000460 chlorine Chemical group 0.000 claims description 16
- 238000004043 dyeing Methods 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 229920003043 Cellulose fiber Polymers 0.000 claims description 4
- 229910052801 chlorine Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 239000000975 dye Substances 0.000 description 15
- -1 Methoxy, ethoxy, propoxy, isopropoxy, butoxy Chemical group 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- VPXCXBHLKDPWQV-UHFFFAOYSA-N 5-amino-2-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C(S(O)(=O)=O)=C1 VPXCXBHLKDPWQV-UHFFFAOYSA-N 0.000 description 2
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical compound ClC1=CN=NN=C1 ORLGPUVJERIKLW-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- SFUJTLIHMWZDTL-UHFFFAOYSA-N 3-acetamido-5-amino-4-hydroxybenzenesulfonic acid Chemical compound CC(=O)NC1=CC(S(O)(=O)=O)=CC(N)=C1O SFUJTLIHMWZDTL-UHFFFAOYSA-N 0.000 description 1
- XPVPPZLJRZSNTD-UHFFFAOYSA-N 5-fluorotriazine Chemical compound FC1=CN=NN=C1 XPVPPZLJRZSNTD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-O hydron piperazine Chemical compound [H+].C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-O 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/046—Specific dyes not provided for in group C09B62/06 - C09B62/10
Definitions
- the present invention relates to new reactive dyes which have a chromophore based on a copper formazan dye and carry a monofluoro- or monochlorotriazine anchor as a reactive group, and their use for dyeing cellulose fibers.
- the object of the present invention was to provide new copper formazan reactive dyes which no longer have the deficiencies mentioned.
- X and R mean e.g. Methyl, ethyl, propyl, isopropyl, butyl, isobutyl or sec-butyl.
- X also means e.g. Methoxy, ethoxy, propoxy, isopropoxy, butoxy or isobutoxy.
- R1 further means e.g. 2-cyanoethyl, 2-cyanopropyl, 3-cyanopropyl, 1-cyanoprop-2-yl, Z-cyanoprop-2-yl, 2-cyanobutyl, 4-cyanobutyl, 2-aminocarbonylethyl, 2-aminocarbonylpropyl, 3-aminocarbonylpropyl, 2- Aminocarbonylbutyl or 4-aminocarbonylbutyl.
- Suitable salts of the copper formazan reactive dyes of the formula I are metal or ammonium salts.
- Metal salts are, in particular, the lithium, sodium or potassium salts.
- Ammonium salts in the sense of the invention are understood to mean those salts which have either unsubstituted or substituted ammonium cations. Substituted ammonium cations are e.g.
- alkyl is generally understood to mean straight-chain or branched C1-C20-alkyl which can be substituted by hydroxyl groups and / or interrupted by oxygen atoms.
- the new copper formazan reactive dyes of the formula I can be prepared by methods known per se. For example, they are obtained by reacting cyanuric fluoride or cyanuric chloride with a copper formazan dye of the formula II in which Y and Z each have the abovementioned meaning, a dye of the formula III in which R2, Y and Z each have the abovementioned meaning, which then results from further reaction with an amine of the formula IV in which R1 and X each have the abovementioned meaning, is converted into the dye of the formula I according to the invention.
- the copper formazan dye of the formula II can also be prepared by methods known per se. For example, it is obtained when the diazonium salt of 1-hydroxy-2-amino-6-acetylaminobenzene-4-sulfonic acid with a phenylhydrazone of the formula V in which Y and Z each have the abovementioned meaning, couples, then produces the copper complex from the reaction product by reaction with copper sulfate or copper chloride and finally converts the acetylamino group into the free amino group by hydrolysis (cf.Houben-Weyl, Methods of Organic Chemistry , Volume 10/2, pages 487 and 488, 1967).
- the new copper formazan reactive dyes of the formula I are suitable for dyeing cellulose fibers. They result in the coloring of medium blue tones.
- the dyes according to the invention have excellent solubility both in water and in up to 30% by weight aqueous saline solutions. They have a very high level of authenticity and high color strength. The color build-up capacity for medium to deep dyeings is particularly high.
- the dyes of the formula listed in the following table are used in an analogous manner receive. Using the usual pull-out method, they dye cellulose fibers in blue tones. The dyes have a very good solubility in water, are lightfast and wetfast and show good stability against oxidative influences.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Claims (4)
- Colorants réactifs du type formazan au cuivre de formule I
X est un reste cyano, un atome d'halogène, un reste alkyle en C₁-C₄ ou alcoxy en C₁-C₄,
l'un des deux restes Y et Z est un atome d'hydrogène et l'autre est un reste hydroxysulfonyle,
R¹ est un atome d'hydrogène, un reste alkyle en C₁-C₄ ou alkyle en C₂-C₄ substitué par un radical cyano ou carbamoyle,
R² est un atome de fluor ou de chlore,
et leurs sels. - Colorants réactifs du type formazan au cuivre selon la revendication 1, caractérisés en ce que X représente un atome d'halogène.
- Colorants réactifs du type formazan au cuivre selon la revendication 1, caractérisés en ce que R¹ représente un atome d'hydrogène.
- Utilisation des colorants réactifs du type formazan au cuivre selon la revendication 1 pour la teinture de fibres de cellulose.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3737536 | 1987-11-05 | ||
| DE19873737536 DE3737536A1 (de) | 1987-11-05 | 1987-11-05 | Kupfer-formazanreaktivfarbstoffe und ihre verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0315046A2 EP0315046A2 (fr) | 1989-05-10 |
| EP0315046A3 EP0315046A3 (en) | 1989-08-30 |
| EP0315046B1 true EP0315046B1 (fr) | 1992-04-15 |
Family
ID=6339828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP88117890A Expired - Lifetime EP0315046B1 (fr) | 1987-11-05 | 1988-10-27 | Colorants formazane cuivrés réactifs |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5004807A (fr) |
| EP (1) | EP0315046B1 (fr) |
| JP (1) | JPH01149859A (fr) |
| DE (2) | DE3737536A1 (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3910649A1 (de) * | 1989-04-01 | 1990-10-11 | Basf Ag | Reaktivfarbstoffe, die zwei oder drei stickstoffhaltige halogenheterocyclen als anker aufweisen |
| US5260431A (en) * | 1989-08-16 | 1993-11-09 | Basf Aktiengesellschaft | Nitroanilinesulfonic acids and the preparation of phenylenediaminesulfonic acids |
| DE3931326A1 (de) * | 1989-09-20 | 1991-03-28 | Basf Ag | Verfahren zur herstellung von 2-(n-alkylamino)-4-aminobenzolsulfonsaeuren |
| DE59010337D1 (de) * | 1989-11-01 | 1996-06-27 | Ciba Geigy Ag | Faserreaktive Formazanfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
| US5241055A (en) * | 1989-12-19 | 1993-08-31 | Basf Aktiengesellschaft | Reactive dyes with a reactive system based on alkenylsulfonyl and benzyl compounds as intermediates therefor |
| US5196573A (en) * | 1990-06-07 | 1993-03-23 | Basf Aktiengesellschaft | Process for the preparation of sulfonated anthranilic acids |
| DE4219421A1 (de) * | 1992-06-13 | 1993-12-16 | Basf Ag | Verfahren zur Herstellung von faserreaktiven Formazanfarbstoffen sowie Aminophenole |
| DE4234900A1 (de) * | 1992-10-16 | 1994-04-21 | Basf Ag | Reaktivfarbstoffe auf Formazanbasis, die mindestens zwei reaktive Gruppen aufweisen, sowie Aminophenole |
| DE19510888A1 (de) * | 1995-03-24 | 1996-09-26 | Basf Ag | Reaktivfarbstoffe mit einem benzoanellierten Heterocyclus als Anker |
| DE19640189A1 (de) | 1996-09-30 | 1998-04-02 | Basf Ag | Reaktivfarbstoffe mit einem heterocyclischen Anker |
| JP3809974B2 (ja) * | 1997-02-28 | 2006-08-16 | 日本化薬株式会社 | ホルマザン化合物及びこれを用いるセルロース系繊維の染色方法 |
| AU5420000A (en) | 1999-06-24 | 2001-01-31 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Reactive dye mixtures |
| GB0212691D0 (en) * | 2002-06-05 | 2002-07-10 | Clariant Int Ltd | Composition for dyeing polyester textile materials |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH612448A5 (fr) * | 1974-12-20 | 1979-07-31 | Ciba Geigy Ag | |
| JPS6067562A (ja) * | 1983-09-24 | 1985-04-17 | Nippon Kayaku Co Ltd | ホルマザン化合物及びこれを用いるセルロ−ス系繊維の染色法 |
| CH667278A5 (de) * | 1985-03-16 | 1988-09-30 | Sandoz Ag | Reaktive formazanverbindungen. |
-
1987
- 1987-11-05 DE DE19873737536 patent/DE3737536A1/de not_active Withdrawn
-
1988
- 1988-10-27 EP EP88117890A patent/EP0315046B1/fr not_active Expired - Lifetime
- 1988-10-27 DE DE8888117890T patent/DE3870151D1/de not_active Expired - Lifetime
- 1988-11-04 JP JP63277527A patent/JPH01149859A/ja active Pending
- 1988-11-04 US US07/267,347 patent/US5004807A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3737536A1 (de) | 1989-05-18 |
| DE3870151D1 (de) | 1992-05-21 |
| JPH01149859A (ja) | 1989-06-12 |
| EP0315046A2 (fr) | 1989-05-10 |
| EP0315046A3 (en) | 1989-08-30 |
| US5004807A (en) | 1991-04-02 |
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